


Teasing the Devil

by AgentDanaZagreusScully



Category: IT (Movies - Muschietti), IT - Stephen King
Genre: Anal Sex, Blood, Choking, Dominant Pennywise (IT), Double Penetration, F/M, Honestly I don’t even know that this is Derry, Masturbation, Non-Consensual Spanking, One Shot, Other, Pennywise gets off on watching people, Spanking, Stalking, Teasing, Tentacle Dick, apologies for grammar, i did not reread before posting, lots of drool
Language: English
Status: Completed
Published: 2019-11-18
Updated: 2019-11-18
Packaged: 2021-02-08 12:14:49
Rating: Explicit
Warnings: Rape/Non-Con
Chapters: 1
Words: 7,489
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/21475855
Author URL: https://archiveofourown.org/users/AgentDanaZagreusScully/pseuds/AgentDanaZagreusScully
Summary: After a long week of work, you just want to go home and relax. After you "relax" a few times you find that someone has been watching you from the shadows.
Relationships: Pennywise (IT)/Reader
Comments: 13
Kudos: 163





	Teasing the Devil

**Author's Note:**

> This is for you Clown Fuckers on Tumblr!
> 
> My first Reader piece so bear with me~

It had been an extremely long week and as you drove home from work after your shift, the sun was already on its way down. The sky was painted red and the clouds were like angry orange flames on the horizon over the treetops. By the time you reached your home, the sun would have hidden away, done until it was to rise at dawn. It was exhausting, the sun going down so early now as the nights grew longer with season’s change. You rolled your shoulders as you slowed to a stop at an intersection a few minutes from home. What were you even going to eat tonight? It would be so nice if for once everything just worked out. Maybe you could have someone at home to cook dinner for you, rub your back or just fucking listen to your horror stories of work. 

Pulling out of your mind fog, you made the last leg of the way home and parked in your space in front of your little apartment. It wasn’t much, and the neighborhood wasn’t the nicest but it was yours and that was all that mattered. The walk to your door was not too far of a walk from where you had parked, as was the nature of assigned parking in a complex such as this one. The path was cast in shadow but the lights had yet to come on, you once again rolled your eyes at the changing seasons, something you did not have any control over.

“Whatever...it isn’t like I haven’t walked this path a gazillion times in the past year.” There was no fear of getting lost or stumbling over a planter. Nothing ever changed here and your steps were confident as your shoes crunched on the gravel. Halfway there and the hair on the back of your neck stood up, you stop and turn to get a good look at the dark, _ empty _ path behind you. “I could have sworn I heard someone…” Nope, you were doing that to yourself. You fumbled your keys out of your bag and picked up the pace until you were shoving your keys into the door and barreling your way into your apartment.

Your heart was beating out of your chest now as you leaned against the door and tossed your keys onto the dingy old couch to your left. You were so tense right now that your jaw even hurt. “The hell is wrong with me right now?” You locked the door and pushed your fingers through your hair. “I need to relax, I’m off for the next two days and I am not letting this week from literal hell ruin that for me.” You shook your arms out and approached the medium-sized fish tank to peek in on your cichlids. As usual, they were fine and colorful doing the thing that fish do the best, swimming. Having pet fish was not like having a dog or a cat, but they still brought you some joy in life and that was all that mattered. 

With a deep breath, you headed down the hall and turned the heater up on your way to your bedroom because it was a lot colder than you thought it was going to get today. The first thing you did when you got to your room was flop onto your stomach atop your comforter, legs hanging off the bed uncomfortably. You groaned and rolled over onto your back so that you had a nice view of the ceiling and your dust-covered fan blades. Man, you needed to clean those, tomorrow maybe? Probably not. You laughed to yourself then forced your body into a sitting position so you could take your shoes off and changed out of your work clothes. 

A great yawn made your eyes water and you shucked your clothes into the hamper. Another day off chore would be laundry. You shook, standing in your room naked, the heater not yet enough to stave off the cold air. “Fuck it, I’m taking a hot shower while the heater decided to take its time.” You made a buzzing noise with your lips and walked into the bathroom off of your room. As soon as your feet hit the tile you jumped. It was ice cold, but you weren’t sure what you were expecting. You wrapped your arms around your body and quickly turned the shower on all the way to Mount Doom temperature, impatient for the sweet hot water to cover your stressed and aching muscles. “C’mon…” You wiggled your fingers under the water and as soon as it was hot you stepped in and slid the shower curtain closed.

It was a safe little steamy cave you had made yourself, the water hitting your body turning your skin pink and the sound of the shower setting you into relaxation mode. For a long time, you stood under the spray, the water hitting your chest and neck to slide over your tummy and down your legs into the drain. You cupped the water in your hands and splashed your face with a sigh. The filth of work was only partially gone. When you finally started moving it was to grab for soap and a loofa. 

You did good you washed your hair and your body, you even sang a little to yourself in the shower but those had not been the only things on your shower list. You felt your heart flutter a little in anticipation of what you were about to do and closed your eyes briefly as you cautiously listened for anything outside your little bathroom sanctum. Not a sound but you and the shower. For good measure, you peeked out of the curtain and when greeted with peace and solidarity you reached up and slowly pulled the showerhead from its holder. 

You were slow, trailing the showerhead over your neck and chest, free hand following after the spray to cup your breast and tease your nipples. It was so nice to finally just have some you time. Your nipples hardened under your touch and you smiled as you felt the familiar throbbing of your clit. How long had it been since you had just touched yourself? A gasp escaped your wet lips as you teased you little swollen bud with the stream of water. You were quick to pull it away then repeat the same game with yourself before it was too much. Pulling your leg up so that you could place your foot on the side of the tub then putting a hand on the wall to steady yourself, you pointed the showerhead at your sensitive clit. 

Your whole body shook, your legs wobbling as your hips thrust in a dance to both get away from the stimulation of the water and to give yourself more. There was not much you could do to keep the moaning at bay and as you oscillated the stream of water back and forth over yourself you could feel the first mini orgasm tear through your nerves. “Ah…” You throw your head back and take your hand from the wall, pushing a finger into your slick slit. “Mnnnmm…” You were so close to getting another high as you slipped your finger into yourself slowly and planned to slide the second one in when the drain gurgled and snapped you out of your pleasure induced trance. The showerhead slipped from your hand and clattered to the tub, spraying your face with water. 

Your eyes grew wide and you stared at the drain in shock. It had never made that sound before. The water was getting cold as you stood there and glared at the drain and you figured that it was likely time to get out. You shut the water off and groaned, apparently, you weren’t supposed to have such a good time in the shower. It was fine, you thought but your body was still buzzing with need. Even walking out of the bathroom only made the need to fuck yourself even more prevalent as your thighs pressed such sweet pressure over your mound.

Body still covered in water and hair dripping with it you shut and locked your bedroom door even though you are the only one living here. Better safe than sorry really. 

You crawled onto your bed and laid back, goosebumps spreading over your skin and nipples hardening almost painfully. You suck in a breath and let your fingers find their way back to your clit. With your middle finger, you circle it, sending waves of pleasure through you. It’s still sensitive from the shower and you moan happily. “Oh god, I fucking need this.” Your back arches as you slide two fingers into your hot slit, you are a little surprised by how wet you are and you wonder if it had really been so long. You pump your fingers into yourself slow at first, curling them while carefully sliding your other hand over your body with eyes closed. 

The walls of your apartment are not soundproof but they are good enough that you do not feel it necessary to keep most of your moaning to yourself. Besides, you like it, hearing the sounds you make. You work your fingers faster while your other hand squeezes a nipple almost punishingly. Your eyes roll back and you gasp, rocking your hips into your hand and pulling your knees up to allow you better access. The bed creaks as you’re practically shaking, begging to get to that peak. You slip your fingers into your mouth and suck on them before curling your fingers against that special little spot and coming undone. 

\-----

You’re a sweaty mess on your bed, and you can’t even remember how many times you made yourself cum. You can’t believe you just went to town like that, you must have needed it. The week _ had _ been rough and honestly...why the fuck not. It wasn’t like anyone else was going to take care of you like this. You laughed to yourself, still blissful with the endorphins of multiple orgasms. It had been amazing, even though a few times it felt like you were being watched. You hadn’t stopped though...and really, the feeling that some pervert was watching you cum on your fingers made your sex muddled mind all the hotter. 

The sheets stuck to you as you urged your body up from where you hand sunk down flat onto your stomach. After all of that, it was bedtime. It was nearly impossible to flip over and sit up but when you did you stilled instantly. 

From within your now open closet door, staring out from the shadows were two glowing orbs. Frozen to the spot, heart jumping like a rabbit, you watch as a very tall very scary looking _ clown _steps out of your closet, complete with a red nose and white paint on his face. He wore an old looking costume made of dove-gray silk, with frills and bells, and topped with three orange pom-poms down his chest. Had you hit your head in the shower? Was this a dream?! Yellow eyes, still glowing in the dim light of the room stared at you calmly, his face blank as you stared in horrible fascination.

You opened your mouth to speak but shut it quickly as a grin that was impossibly widespread across his face revealing buckteeth like a rabbit and allowing for a glob of drool to roll out of the clown’s mouth. “Hellooo~ there [Y/N].” You would not have expected the voice that came from his lips to have belonged to him but you figured that your mind was being funny...it was a dream after all. That was how the clown knew your name anyway. “You look surprised to see me,” He tilted his head to the side, the red of his coiffed hair falling into the light of her bedside lamp, “but haven’t you been teasing me all night?” An almost childish laugh shook the clown as he began to stalk closer to where you were on the bed. “You know, [Y/N] it isn’t nice to tease people.”

“I- I wasn’t teasing anyo-” You started.

“Oh! But you were, [Y/N]. I’ve been watching you all night.” Your cheeks flamed red and you could not fight the urge to scramble further up into your bed towards the headboard. “Ooh, your nasty little thoughts as you got out of your car, thinking about how you would touch yourself, pleasure yourself in the shower.” He shivered with laughter again and more drool slid over his lips and down the front of his suit. “Mmmm, and then you spread yourself for me to see. You knew I was watching you, you _ felt _ it [Y/N]. Didn’t you…” He was at the foot of your bed now and you had scooted up as far as you could, tucking your legs under yourself in some sort of self-preservation technique. “Oh hohhooohahahhaa! Cat got your tongue? B-But you were so loud before! Mmmm such delicious sounds you made, so slick...so _ wet _.”

You were shaking your head but you could not deny that for some sick reason your body was reacting to this clown telling you that he had been watching you masturbate all night. That he could read your mind! “I wasn’t doing it for y- you.”

He jerked his head to the side and frowned suddenly. “Not for me? But then for who?”

“I don’t even know your name….” You countered.

He grinned once more and pounced onto the bed sending your body into distress and...arousal. “[Y/N] meet Pennywise,” his hand snapped forward and yanked your foot down towards him. “I hope you aren’t tired [Y/N]...becasue you look tired.” His smile kept widening as you began to try and pull your leg out of his vice grip. “But see here, Pennywise isn’t tired. He isn’t tired at all.” His voice dropped into a rumbling growl. “And he doesn’t believe that you weren’t teasing him all night, screaming and moaning, so wet for him, all for him.” He licked his lips, drool pooling next to your leg as his other hand snaked out with blinding speed grabbing up your other ankle, spreading you wide for him to see. You felt your walls clench in betrayal and he must have known because he laughed again as you involuntarily quivered for him. 

“Please…” You attempted to fight him again, but there was something about him that was drawing you in like a moth to a flame. He held your legs fast and the only options you had were to scoot closer or keep yanking though you were beginning to see he was not going to let you go. 

“If you can fight, you must not be tired.” He looked ready to burst with excitement and then shook, bells on his costume jingling like Christmas. He grinned, “Christmas? Not today, Oh but you’ll like this present.” He made your choice for you then as he pulled you down so fast your back popped uncomfortably. His face was at the apex of your thighs his eyes studying your swollen folds. Pennywise took a deep breath through his nose as he pressed his face in close to the heat radiating from your slit. You shivered at his rumbling growl. “I’m so glad you aren’t tired [Y/N] because **it’s my turn to have fun!**” 

You tried to rip yourself away from him only too be hushed by something hot and slick burying itself deep inside of your raw slit. The pleasure and slight pain of being filled by what you could only guess was his tongue caused you to groan, the fight forgotten for a brief moment of ecstasy. The appendage wriggled inside of you, finding every spot you knew you liked and spits you hadn’t known you liked. “N-noo…” Your body was betraying you even with how spent you already were. But you couldn’t just let this happen. Thoughts of how to escape filled your brain.

Penny’s ripped his tongue out of your slit quickly, a string of saliva and your slick bridging the two of you as you gasped at his sudden exit. He began to growl then, and the sound was like a combination of an alligator and a wolf. He felt your body tense and prepare to flail, his growl growing deeper, more threatening as his golden eyes flared. The tip of his tongue circled your clit and skirted your folds as he watched you react to him. He grinned as a whimper left your mouth, his gloved hands tightening on your thighs. “It would be wise if you did not fight me [Y/N]. I will have you one way, or another.” He grinned then and his buck teeth were gone, replaced with fangs. “Pennywise can make it feel good for you too [Y/N] or we can do it the **hard way**.” Seeing his teeth was supposed to make you scream, but all you could feel was the drool from his tongue slipping out of your slit as you shivered in desire. 

“I won’t f-fight.” It was humiliating to say, almost as humiliating as being aroused by a clown eating you out. This was better though, if you did not let him have his fun he would surely have his way and have a nice snack on your flesh in the literal meaning. As important as it was not to get yourself eaten, you were finding the lack of being filled by something more prevalent in the forefront of your mind. 

The clown threw his head back and roared out a peal of laughter that was near deafening. Your body shook in his grasp and soon it shook with more. Hands still holding you and head still leaned back with laughter, Pennywise got on his knees, pulling your hips up with him until you had to hook your legs over his shoulders. The position he had you in now was not the most comfortable and you felt the blood rushing to your head as he stopped laughing and snapped his face forward. He grinned then let his tongue loll out of his mouth.

The sight of his glistening tongue made you shiver and his eyes watching your reactions made your core ache. Why wasn’t he doing anythi-

His eyes flashed and once more he buried his tongue inside of you. It writhed inside you as if it had a mind of its own and your desire burned like a torch within you. He ripped the moans from your lips as his arms tightened around your body, deft fingers clothed in silk sliding down to grope savagely at your breasts. 

He was messy as his tongue reached inside of you growing impossibly long as it coiled and more than your own juices were sliding down towards your face. His drool, sweet-smelling like cotton candy was slowly dripping over your stomach and chest. Though you didn’t recall having a fetish for it, it was hot. You were writhing, trying to hide your face from him only to be growled at. He wanted to see you and to see the faces you made as you screamed for him. 

Something happened then that had you nearly crying as an orgasm exploded from you. Pennywise locked his mouth over your mound, knowing the face he had seen again and again earlier meant you were close and that you had just made it once more. You felt something writhing over your clit, tickling it as it wrapped around it and tugged with gentle precision. That new appendage was not alone and something else in his mouth curled out. You saw his eyes roll back in his skull through your own watery eyes as another wriggling tendril slid between the cheeks of your ass and began to prod at your hole. 

Your eyes grew wide and you began to fight against him again. It was no use however and the pressure you felt building was about to crash down over you. The tendril at your ass slid further in and was joined by another trying to massage you open. “N-no! Not t-there!! Aaah!!” Your body tensed as you felt everything unravel. All at once Pennywise pinches your nipple hard, the tendril at your clit wrapped tight around the swollen nub and the larger of the two at your ass delved into you. You screamed unlike you had ever made yourself scream and the dam of your arousal broke. 

Wetness gushed from your core and coated your thighs, it mixed with the drool that he produced with impunity and ran down your chest and over your ass and back to soak into his costume and your bed. Wave after wave of euphoria encompassed your body and a ringing grew in your ears. He was sliding his tongue in and of your slit, slurping up your juices, making such lewd sounds that your face was on fire with embarrassment. A gasping sob tore out of your mouth as he reached for your neglected nibble and pulled at it roughly.

Laughter was beginning to shake him as you began to cry from the over-stimulation of your clit which was still being tended by the other strange appendage from between his lips. The laugh made your toes curl and you made to look away. He pulled at your nipple harder until you looked at him, those yellow eyes staring deep into your soul. “Ple-“ you shivered, “Stop, please sto-“ He growled at you, the vibrations shaking you. But you didn’t want him to stop, he knew it as well as you did. You wanted more. Even if you knew that it would hurt, even if your body was already so sore and tired from what you had done to yourself, you wanted him. 

He laughed again and slowly, so painfully slow you were almost unsure of what he was doing, Pennywise pulled all of the writhing tendrils and his tongue into his mouth. His face was glistening with your arousal, and his frilled collars were damp with it too. “Mmm,” he giggled, “You taste so yummy [Y/N]!” He grinned and the fangs he had used to scare you into compliance returned to shine in the light of your bedside table. “**Do you feel as good as you taste?!**” The clown's voice was so deep, possessive growling tangling with his words.

There was no time to answer before he shoved you further up and dropped you onto the bed. He flipped you over with ease and pushed your face into your pillows, his hands tugging your hips into the air for what he had planned to do to you next. There was only the briefest of moments where his hands were not upon you but those few seconds passed so agonizingly slow. You needed him, needed to feel him inside you again, whatever he was planning to give you. 

His warmth radiated behind you as he looked at you leaned over for him, you could feel his eyes roaming over your body, gazing at your dripping folds. The clown’s hands were on you then, his touches feather-light as he started at your toes. Goosebumps followed the path of his fingers as he ghosted them over the bottoms of your feet up to your calves and over your thighs. He paused as you sucked in a breath in anticipation of him touching your aching nerves but he did not give you what you wanted. He flattened his hands on your rounded cheeks and pressed his thumbs into them as he slowly pulled them apart. You gasped, cold air hitting your wet core as your walls clenched in need. He repeated this motion, pulling your folds apart so he could watch you shiver as your sex made wet little sounds. You turned your head to the side “Please…,” you begged breathlessly before biting your lip at how desperate you sounded.

_ Smack. _

Your ass stung as a gloved hand came down hard on your now reddening cheek. You look over your shoulder then in shock and saw the grin dripping with drool on his face. He had spanked you! The realization caused you to try and push yourself up and he smacked you again. “No, no, no, [Y/N] did I not tell you that it was **my** turn to have fun?,” He chastised at you with a sing-song voice. “I decide what happens little one. You were rude, teasing ole Pennywise for hours on end even though you could feel him watching.” He smacked your ass again with a grunt then caressed the mark with cool fingers. “But not once did you invite him to play with you. Not at all [Y/N].” _ Smack _ . “So now I’m going to have my fun and you get to plaaaay along like a good little ** toy**.” You saw as he raised his hand high, squeezing your eyes tightly shut as you feared the pain he was going to inflict. “Let’s see how good you are at counting [Y/N]. Count with me!” He barked out a laugh then down came his hand. “One. Two. Three!” 

You were too stunned to count and a growl fell from his lips that sent a shiver of fear and heat over your skin. His hand came down on that same cheek several more times before you felt him curl over you and roughly tangle his fingers in your hair.

Hot drool pooled on your back as he yanked you back by your hair so that you had to arch to see him, it felt as if he were pulling the hair out of your head as he twisted his hand. **“You aren’t counting [Y/N]! Count or you won’t like what happens.” **Pennywise spat it out as he pressed his hips hard against you. Something was writhing in his suit but you did not have long to think about it before he threw you down and pressed your face back into the pillows. “Count with me~~” He sang at you with a voice so different than the one he had just growled at you in.

His deranged giggle made your walls clench, begging to be filled up again and when his hand came down on your rear you counted with him. You slipped up a few times as arousal started to replace the pain you were feeling but he did not stop until he landed one last stinging blow on the count of fifteen. You did not dare beg him for anything, Pennywise planned to use you as he wished and you were to do as he said. 

You were his toy.

“Good little [Y/N]. Maybe I could forgive you for being rude?” His hand caressed your swollen skin. “Would you like that?” His voice was soft, cooing at you as if you had pleased him. In a way, you figured that you had. He massaged your hips with a grin then without warning slipped two long fingers into your waiting cunt. “Maybe I will reward you for such exemplary counting on your part?” You gasped, he had slipped in so easily the pressure feeling so fucking good. You needed more, he had to move his fingers or you were going to fall apart. He did not move and you whimpered, pushing your hips back to feel more of his fingers. His free hand was like steel and his grip on your hip did not allow the movement you so desperately craved. The clown tsked once before curled his fingers down to press just so on your g-spot.

“Oh god!” A jolt of blissful euphoria erupt from the spot he was pressing and it was accompanied by a pleased giggle on his part as you squeezed his fingers inside of you. “Mo-

He pressed firmly on the spot again making you lose the words you were about to say. “Don’t be greedy, good things come to those who wait!” Pennywise scissored his fingers inside of your hungry sex, sliding them in further slowly before slipping them out of you. He simply laughed at your moan of distress. “Would you like a taste sweetling?” 

You rolled your eyes to look back at him and saw the dampness of his gloved fingers. Moving them for you to see, he showed you just how sticky and wet you were for him. His eyes glared into your own expectantly and you nodded quickly. The fact that he was asking you at all was a gift you would not turn down. But you also were hungry to please him. The drool that dribbled down from his lips made it clear that he was pleased with your answer. Again he pressed his hips to yours, but the writhing that you had felt before was gone, replaced instead with a more familiar feeling. He was erect behind all of that silk and ruffle and the way he felt against your ass told you that he was _ very _ large. He had been getting you ready for him this entire time...and you were not sure how to feel about that. 

“You should feel thankfuuul~” He pressed his fingers wet with your juices to your lips, expecting you to make truth of your earlier answer. It was going to take getting used to, his ability to get in your head. You watched him as you parted your lips for his fingers, wanting to see his expressions when you sucked on them circling your tongue around the digits. Under the taste of your sex he was sweet like candy with an earthy undertone you could not place. He allowed you to shift so that you could more easily access his fingers, you bobbed your head as you sucked and moaned around him. The erection behind you shifted, changed, and you paused. The clown’s lips twitched, you did not think he wanted you to stop what you had been doing. 

Curiosity made you do something absolutely stupid, but you wanted to see his face change, to feel the thing within his trousers move again. Slowly you gave the clown what he wanted, you bobbed your head, moaning for him again as drool slid down over his chin. Then, as if you were an animal, you bit down hard on his fingers. 

Something you had not quite expected happened then. Pennywise groaned, a shiver ran through his body and the grip on your hip grew painful, There was a ripping sound and what you guessed were nails dug into your hip. Your mouth jerked open at the pain of his nails pressing into your soft skin. He shivered again and the bells on his costume jingled violently as he shook. You were afraid, had you messed up? Had you done something you could not go back from?

The hand you had bit gripped the back of your neck and pressed you down harshly into your bed. He was growling now and the bulge in his pants seemed to grow, writing again now as it had before. Pennywise pulled his hand back from your neck and trailed sharp claws down your spine hard enough to raise welts but not to make you bleed. The same could not be said for your hip, the burning pain of his nails there told you that you were likely bleeding.

As he had done before, the clown spread your cheeks, unlike last time though...he was done playing.

You howl in painful bliss as the wriggling appendage you had been feeling bursts through the clown’s costume and impales you suddenly. You could not breathe as nails dug into your hips and the molten tendril trashed about inside of you. There had never been a time in your life you had felt so much pleasure nor pain, and absolutely not at the same time. He pulled back slightly and you took that moment to gasp for air, to claw at the sheets under you though there was no getting away. Light burst behind your eyes as he slammed his hips back flush to yours with a wet squelching sound. Why was there no air in the room! It felt as if you were suffocating. Your mouth gasped like a fish out of water and the clown behind you growled, slamming into your tight heat again and again with something that had a mind of its own. It reminded you of his tongue but this was so much worse...better? 

Each slap of his hips against yours sent the sound of wet slipping and grinding echoing in the room to mix with your chorus of whimpering moans and his pleasured grunts. The force of his hips pushed you further up the bed and made your back bend painfully. Tears were rolling down your cheeks now and drool pooled beneath you on your pillow. If there were words to say, you could not have spoken them. He was relentless, taking whatever he wanted from your body. But it felt so good, how could something like this feel as it did? He was impaling you over and over, stretching you so far you knew that you would not be able to walk comfortably for a good few days. Why you? Why had he been watching you?

**“Why not?”**

Your whole body shook as he spoke, sweet molten heat was pooling in your core and his voice made your eyes roll back. _ Please. Please. Please. _You begged him for something to let the floodgates open to send you over the edge. And as you had asked it, you received it. 

The tendril within you split, stretching you wider inside and finding every single spot you needed to be touched at that moment. You screamed as he slapped your ass, an orgasm ripping you apart like he was. With your wetness dripping down your legs, your core pulsed and fluttered with hunger as it attempted to pull from him what he had wrought out of you. 

“Good little toy, cum for me. Tell me that I feel better than your filthy little fingers.” A few of the seeming mass of tentacles within your dripping slit slid out of you and began to caress your folds. “You will never find anyone that will make you feel like this [Y/N], wouldn’t you like to be my toy _ forever _?” Two little tentacles found your clit and began to rub it between them. You could not answer him and he knew it, but he could see in your head that you knew he was painfully correct. No one, especially not yourself, could make you feel like he was making you feel tonight. 

A word finally jumped out of your mouth when a thick tentacle found the tight ring of muscle that was your ass and began to prod it experimentally. “NO!” You made to get away from him, really get away from him, afraid of the same feeling that was slitting you in two within your slit repeated in your ass. You squirmed even though the feeling of the appendage slipping into you gently was like heaven. 

“And you were being so goood~ for me. I’m afraid I will have to punish my new little toy.” A hand slid down your back and wrapped its way around your neck. His claws were still out and they dug into you as he pulled you up. “I thought that you understood how we were supposed to play this game [Y/N]. I would hate to have to **break you**.” He squeezed your neck threateningly making you arch your back as he restricted your airway. “Do not fret, Pennywise will make you a happy little pet.” He grinned and the tentacle that had been simply toying with the idea of entering you slid home into you. The clown shook with a groan, now seated within both of the holes you had to offer him. You watched him as much as you could in your position as his head lolled back and his teeth grew sharper.

You were gasping now, his grip on your throat tightening the longer he remained still. You wanted to beg him and apologize for trying to run away, but you could not speak. There was not much that you had in your arsenal at the moment so you did what you could. Carefully, so as not to have your hips impaled further with his nails, you ground yourself back into him. You coaxed him to move, to do anything, to make you cum again. The tentacles that you could not see but could most definitely feel wriggled. You shiver and gasped out a moan.

Pennywise was shaken from his stupor then, drawn back from whatever thoughts had drawn his mind away. His head came forward like a roller coaster slowly climbing an incline then dropped forwards with a monstrous growl. His eyes were ringed with red again and his teeth still glinted dangerously at you. There was no going back now that you had instigated his movements again.

The clown pulled back slightly and paused. “I’ve decided to make you an offer you cannot refuse.” He giggled, “But first let us see if you will survive!” Pennywise snapped his hips forward and began to set a relentless pace, pounding into you with such strength and fervor that you were convinced he was going to break you. Bruising was guaranteed, tearing...absolutely, survival, yet to be determined.

Your nerves were shot and you were unsure if the next orgasm he brought you too would be your last. Tendrils continued to play with and roll you poor swollen clit between them and it was more painful than pleasurable. You let him use you until your throat was raw from the screaming you were doing for him. He made you look into his eyes as he tore you apart and smiled at the tears streaming down your face. The clown had decided that he was indeed still mad about your attempt to get away and as such he was doing his best to punish you. Even through it all, you could feel the telltale pressure of an orgasm building. Up and up he pushed you until you were almost there with fluttering eyes and shaking legs. 

Pennywise pulled out of you and flipped you onto your back on the bed. The orgasm ripped away you offered the clown a hiccuping whine and knotted your fingers in your hair as you felt the need to cry. But if for some reason you thought he was done, you were painfully wrong. As you watched with watery eyes, the tentacles which you now saw were as pale as the paint on his face coiled together to form one slippery tendril with a blunt head. He grabbed your hips and pulled you to him in one fluid motion and slid home between your sore folds.

He was slightly slower now, more careful as he looked at your body underneath him. You watched as he shivered and shook like he was going to burst at the seams and you slowly began to realize he was holding himself back. Pennywise rocked his hips into you and made sure to hit every happy little bundle of pleasure inside you as he did. He wrapped your legs around his waist and held them there because at this point your body was not in the state to listen to your whims. Your moans were echoed with his grunts and when his pace began to quicken he allowed you to look away from him so that your eyes could roll back.

Your little bubble of euphoria that he had stolen from you a little ago as he had pulled out of you began to swell inside of you and you hoped that he would allow you one last orgasm, no matter how painful it might be for you to have. A clawed hand slid up from your waist and over your stomach until it rested over your chest. His thumb played with your sensitive nipple and you gasped, body quivering as the pressure built within you. You were so close and your breaths were shallow and quick.

Pennywise’s pace was growing quicker now, and more erratic to boot. The sounds that accompanied the drool from his lips were becoming more inhuman and it felt like he was growing inside of you. “Good little toy….so good for me. So- Good-” He grunted and pressed his hips flush to yours quickly. His words sent you over the edge and you squeezed around him frantically. He roared and snapped his hips forward to drill into you through your orgasm.

And with one last bruising thrust, he spilled his seed inside of you. He poured into you more than you thought could be possible, stretching you full until there was nowhere for the rest of it to go but out. Cum, black as sin spilled out past him and onto the bed beneath you where it was sure to stain your sheets. Gnashing his teeth together the clown continued to thrust into you a few more times before he pulled out with an awful pop. His seed gushed from you and he watch this with a look you could not place. You could only widen your eyes as the clown lowered his mouth to you and began the process of licking you clean. 

\----------

At some point, you must have passed out because you awoke with a start upon hearing a knock on your door. By the sound of birds chirping and sunlight assaulting your eyes, you guessed that it was sometime in the morning. You opened your eyes carefully, expecting your lashes to be stuck together with how much you had been crying last night. Surprisingly enough, there was nothing but some standard eye crusties and when you looked around you were tucked into bed wearing an oversized t-shirt. The thought that last night had been a dream only briefly occurred to you as you attempted to swing your legs out of bed to see who was knocking on your door. Immediately overcome with the worst cramps and overall pain you had ever felt, you fell to the floor with a groan. 

You bit your lip and rolled onto your side with a quiet groan. Real...all real. Opening your eyes, you were greeted with a sight that only further proved the realness of last night's escapades. Next to your bed, tossed to the side was a little bell. If you touched it you thought you might break some sort of spell, or that you would wake up to find this a dream too. Honestly, you didn’t want that, so instead of picking the little bell up, you did your darndest to pick yourself up off the ground and limp your way to the door.

Tears are threatening to spill from your eyes after the journey from your bedroom but you made it to the door and decide to peek through the peephole before flinging the door open. A man, tall and very attractive waits on the other side looking slightly annoyed by how long it took you to get to the door and you decide to open up before he can knock again.

“Hello? C-can I help you?” Your voice is shot and you make a note to put some tea on when you get this guy to go away. 

The man in front of you towers over you, over six foot, to say the least, with shockingly bright blue eyes and full lips that honestly made you a little jealous. “Hey, I’m sorry to be bothering you so early in the morning but could you tell me where apartment 201C is?” His voice was so nice you could melt.

It honestly took you a moment to process before you were leaning out the door and pointing to the apartment next door. “Sorry about that, the numbers didn’t get put back up when they repainted the door.” You offered him a tired smile and nodded. “Well good da-”

“Wait!” He grabbed your door and stopped you from closing it. You eyed his hand then blinked up at him to wait for him to speak again. “My name is Robert Gray.” He stuck his hand towards you with a grin. “I guess you’re my new neighbor.” At your confusion, he chuckled. “I’m moving in next door.”

You nodded slowly and took his hand. “Oh...well...welcome to the neighborhood Robert.” You smile pleasantly but honestly, you need to sit down. He squeezed your hand then pulled back to tug a key out of his pocket and unlock the door that you had pointed to. “I guess I’ll be seeing you around…”

“Oh- I hope so.”

**Author's Note:**

> Thank you so much for reading!


End file.
